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- W2950470906 abstract "The thermal cycloisomerization of some alkylacetylenes was investigated in a tubular quartz reactor. At 570°C 1-hexyne (1) rearranges to 3-methyl-1-cyclopentene (5) with a selectivity of about 27 by a reaction sequence including an acetylene-vinylidene rearrangement and 1,5-C,H insertion of the intermediately formed alkylidenecarbene species. 5-methyl-1-hexyne (2) behaves analogously forming 3,3-dimethyl-1-cyclopentene (6), while 2-hexyne (3) provides 1-methyl-1-cyclopentene (7) indicating that the acetylene-vinylidene rearrangement is obviously not restricted to 1,2-H shifts. The mechanism of the cycloisomerization of alkylacetylenes is investigated by means of D-labeled parent alkynes. The results show that the unimolecular cycloisomerization via alkylidenecarbenes obviously can be an important channel despite the dominance of a radical chain course." @default.
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- W2950470906 date "1989-07-11" @default.
- W2950470906 modified "2023-09-26" @default.
- W2950470906 title "ChemInform Abstract: On the Thermal Cycloisomerization of Long-Chain Alkylacetylenes in the Gas Phase." @default.
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- W2950470906 doi "https://doi.org/10.1002/chin.198928079" @default.
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